In 1998–1999 Stewart was the head coach of the New York Islanders. He then moved on for one tumultuous season as the head coach of the Barrie Colts in the Ontario Hockey League. The roster that year included Ryan Barnes, who was charged with assault with a weapon after a stick-swinging incident during a game in October. Later in the season, 3 of the team's other players (Nick Robinson, Mike D'Alessandro and Aaron Power) were charged with sexual assault. Finally, Stewart himself made headlines and was banned from entering the United States for twice smuggling a Ukrainian-born player over the Canada–United States border in the baggage compartment of the team bus. After that, Stewart moved on to coach in Germany.